Synthesis of the furanone analogues of goniotriol with antitumor activity

• Main Authors: Victor, 饒中書
• Other Authors: 游錫榕 沈建昌
• Format: Others
• Language: zh-TW
• Published: 2008
• Online Access: http://ndltd.ncl.edu.tw/handle/61300762568546114941

碩士 === 中國文化大學 === 應用化學研究所 === 96 === Goniotriol is one of the styrylpyrone compounds which were isolated from Goniothalamus sesquipedalis and showed inhibitory activity on several human tumor cells. In this thesis, we propose a synthesis of the furanone analogues of goniotriol in order to inverstigate their antitumor activity. Methyl (R)-mandelate was chosen as the starting material, which was treated with TBDMSCl and imidazole in DMF to give a hydroxyl protectded compound GF-1. Ester GF-1 was reduced by DIBAL-H and the oxidized to provide aldehyde GF-3. The Wittig reaction of the aldehyde and methyl (triphenylphosporanylidene)acetate afforded GF-4. The double bond was oxidized by Sharpless asymmetric dilydroxylation to give diol GF-5, which reacted with chloromethyl methyl ether to afford GF-6. The ester was reduced to alcohol GF-7 by DIBAL-H and then was transformed to aldehyde GF-8 via oxidation with PCC. The nucleophilic addition of GF-8 and trimethylsilylacetylide provided two stereoisomers, GF-9 and GF-10, which were treated with base to remove the trimethylsilyl group to give GF-11 and GF-12. GF-11 or GF-12 can react with methyl chloroformate to afford an ester and the triple bond can be hydrogenated to yield a cis double bond. After removal of the protecting groups and lactonization, the furanone analogues of goniotriol will be obtained.